Monthly Rentals in Siesta Key

(105 rentals)

Looking for a tropical getaway on Florida’s Gulf Coast? Our monthly rentals in Siesta Key offer the perfect long-term escape in one of the most beautiful beach destinations in the world. Whether you're planning a winter retreat or a summer vacation, Siesta Key’s pristine beaches, vibrant nightlife, and outdoor activities make it an ideal destination.

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$516

avg/night

$516
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

BREATHTAKING GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE BEAUTFUL CRYSTAL SANDS COMPLEX. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$283

avg/night

$283
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Home away from home.... I enjoy my coffee and cocktails at waterfront lanai and when I travel, I would love someone to enjoy it as well. I live in this condo, therefore, this unit has everything you may need and more. Boating, fishing, paddle boarding, kayaking, biking to Siesta Key Beach or free trolley ...

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Property Type

Siesta Key Condo

Featured review

"Spectacular"

We’ve been vacationing in Sarasota/Turtle Beach for over 10 years. This condo is our ABSOLUTE FAVORITE! Very nicely decorated & accommodating. We love that it is located on the bay. It is GREAT for fishing ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$516

avg/night

$516
avg per night
View Details

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

SPECTACULAR VIEWS FROM THIS 2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. THE CASA MAR COMPLEX OFFERS 2 POOLS, TENNIS, WIFI, (SIESTA 4- RENT DOES NOT OFFER TECH SUPPORT), COMMUNITY LAUNDRY ROOM, AND 1 COVERED ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2.5 bathrooms

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$643

avg/night

$643
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

***FALL SPECIAL -- 15% OFF OCTOBER - DECEMBER 15TH*** Luxury at its finest in this 1600 sq. ft. 2006 built Crescent condo complex. This Unique 2 Bedroom 2 Bath on the 2nd floor of the complex is a quiet and peaceful setting and opens up directly to one of the two pools through an additional large outside ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$411

avg/night

$411
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Luxury water view vacation home only a few minutes from one of the best beaches in the world and #1 in the USA! Like so many others have, make this a yearly vacation spot for you and the family.Our home, located on Siesta Key, with breathtaking intercostal water views is fully furnished with all the ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$600

avg/night

$600
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful Crescent 2 Bedroom Penthouse Unit with partial Beach views, large balcony overlooking pool area in the center of the building and additional Beach Front pool offered. Appointed with Hardwood Floors, Large kitchen and laundry in unit, 3 TVs, Wifi internet( Siesta 4 Rent does not offer tech support). ...

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Property Type

Siesta Key Condo

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Siesta Key Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$281

avg/night

$281
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

Featured review

"We Keep Coming Back"

It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring ...

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Siesta Key Condo
1 BR | 1.5 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1.5 bathrooms

$508

avg/night

$508
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

**Any advertised discounts on website do not apply to this unit*** UNIQUE 1 BEDROOM TOWNHOUSE OVERLOOKING THE BEACH, 1 BLOCK TO SIESTA VILLAGE, 3 STORY UNIT WITH GARAGE ON 1ST FLOOR AND WASHER/DRYER, BALCONY, MEXICAN TILE FLOORS, KITCHEN, SPIRAL STAIRCASE TAKES YOU TO THE MASTER SUITE ON THE 3RD FLOOR, ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$445

avg/night

$445
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Comfortable private 3bedroom 2 bath home, open concept floor plan. The hone has a salt water heated pool. You can bike ride or walk to the main siesta key beach pavilion. There you can play pickleball or enjoy the service at the snack bar or continue out to the white quartz sand and clear waters of the ...

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Property Type

Siesta Key House

Featured review

"Definitely more than 5 stars for this property"

I’ve rented several Siesta Key properties, but this is definitely my favorite. The home is located very close to the public beach down a quiet cul de sac. The neighbors were all friendly and the area ...

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Siesta Key House | On the beach
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms
7 reviews

Distance to beach: 300 feet to Siesta Beach

$780

avg/night

$780
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

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Property Type

Siesta Key House

Featured review

"Great property on the sand."

We had a great week despite the heat of summer. This house although dated was clean, cool and comfortable. It was a two minute walk through the back yard to the sand. We had a few minor house keeping ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$550

avg/night

$550
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME STAY AND RELAX IN THIS BEAUTIFUL 2 BEDROOM / 2 BATH CONDO LOCATED IN THE PALM BAY CLUB TOWER OVER-LOOKING THE WORLD FAMOUS SIESTA KEY BEACH, ( SAME SIZE AND VIEW AS PENTHOUSE UNIT.) ALL THE AMENITIES. FROM THE TILE FLOORING, GRANITE COUNTERTOPS AND STAINLESS STEEL APPLIANCES TO THE LEATHER FURNITURE, ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$442

avg/night

$442
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Siesta Key living in this charming 2nd floor duplex in Siesta Village. This gem offers a perfect blend of comfort and convenience. Nestled in the heart of the village. this unit offers 2 bedrooms and 2 baths with a large shared pool with the unit downstairs. This quaint unit features a washer/dryer ...

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Property Type

Siesta Key Condo

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Siesta Key Bungalow
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$283

avg/night

$283
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

Featured review

"A Great Home Away from Home"

I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors ...

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Siesta Key Condo
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
2 reviews

Distance to beach: 0.0 miles to Siesta Key Main Beach

$221

avg/night

$221
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

PENTHOUSE WATER VIEWS! RESORT LIVING ON SIESTA KEY at Harbor Towers Yacht & Racquet Club, gives you the best of both worlds - Beach and Resort! PENTHOUSE CONDO WITH WATER VIEWS: Spacious 1 bedroom Condo with 2 Queen beds - one queen bed in spacious Bedroom, and second Queen Bed is a brand new ...

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Property Type

Siesta Key Condo

Featured review

"hurricane"

Unfortunatley we cancelled are vacation because of the back to back hurricanes Siesta Key suffered. We were very disappointed. The owner, Sue, was such a pleasure to work with. We would love to be able ...

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Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$489

avg/night

$489
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

CHARMING 3 BEDROOM PRIVATE HOME LOCATED IN THE QUIET SUB-DIVISION OF SIESTA ISLES. RELAX ON VACATION WITH ALL THE AMENITIES OF HOME. PRIVATE POOL, 2 CAR GARAGE, WASHER / DRYER, CHARCOAL GRILL, AND MUCH MORE. HOME OFFERS 2 LIVING ROOMS, ( ONE WITH LEATHER FURNITURE AND 53" T.V.), 6 T.V.'S, 2 ...

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Property Type

Siesta Key House

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$636

avg/night

$636
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

THIS 3RD FLOOR CONDO WAS RECENTLY REFURNISHED WITH ALL ROOMS GETTING ALL NEW FURNITURE AND FURNISHINGS AND ALL BEDS HAVE 800 COUNT VERA WANG HOTEL- STYLE SHEETS. THIS UNIT ALSO HAS A FULLY RESTOCKED COOKS KITCHEN, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, AND MUCH MORE. 2 BEDROOM / 2.5 BATH, OVERLOOKING ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$442

avg/night

$442
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Siesta Key living in this charming ground floor duplex in Siesta Village. This tropical oasis offers a perfect blend of comfort and convenience. Nestled in the heart of the village, this unit offers 2 bedrooms and 2 baths with a large shared pool with the unit upstairs. This clean and bright ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$714

avg/night

$714
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

EXPERIENCE LUXURY AT IT'S FINEST IN THIS STUNNING 2ND FLOOR CONDO WITH PARTIAL GULF VIEW FROM SIDE BALCONY. BACK PATIO OPENS UP TO ONE OF THE TWO POOLS AND FEATURES A GORGEOUS OUTDOOR KITCHEN. KITCHEN HAS GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, AND NEW WOOD FLOORING IN ALL BEDROOMS. LARGE ...

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Property Type

Siesta Key Condo

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Siesta Key House
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2.5 bathrooms

$642

avg/night

$642
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and a one-car garage and washer and dryer. Beautiful hardwood floors, solid wood cabinetry and sleek granite countertops. ...

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Property Type

Siesta Key House

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$264

avg/night

$264
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Spectacular, modern 1 bedroom , 2nd Floor unit in Siesta Key Village offers great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 1 flat screen TV. Complex offers heated community pool and laundry ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 3RD FLOOR AND IS A 2 BEDROOM / 2 BATH UNIT. COMPLEX OFFERS HEATED POOL, TENNIS, FULL LAUNDRY FACILITY AT COMPLEX, COMMUNITY ROOM AND A SMALL PIER. UNIT HAS WOOD FLOORS THROUGHOUT , LEATHER FURNISHINGS AND ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$285

avg/night

$285
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 4TH FLOOR AND IS A 1 BEDROOM / 1 BATH CORNER UNIT. WASHER/DRYER IN UNIT. COMPLEX OFFERS POOL, TENNIS, 1 ASSIGNED COVERED PARKING SPACE. UNIT HAS 2 TV'S, DVD. HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$429

avg/night

$429
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

*** 20% off weekly rates for all remaining weeks from Dec 15th 2024 to April 30th 2025*** Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 2ND FLOOR AND IS A 2 BEDROOM / 2 BATH REMODELED UNIT. COMPLEX OFFERS A NEWLY RENOVATED POOL AND POOL DECK, TENNIS, COMMUNITY ROOM AND A SMALL PIER. UNIT HAS TILE IN THE MAIN TRAFFIC AREAS WITH CARPET IN ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$576

avg/night

$576
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

*** JANUARY 2025 SPECIAL- $11,500/month or $3000/wk for 1st two week or last two weeks*** Completely Remodeled Beachfront 11th Floor unit at Crystal Sands. Gulf views from each bedroom and living room south on Crescent beach. (The view in picture #3) is the view from your screened lanai. Elevator down ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to our vacation oasis. We love the peaceful, friendly vibe of the Bay Oaks Community and hope you do as well. Our two bedroom, two bathroom second floor condo unit has been recently upgraded with new living and dining room furniture and new bedding in relaxed but upscale style. The complex sits ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$829

avg/night

$829
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

This lovely penthouse condo is in one of Siesta Key's newest complexes (built in 2006). The Crescent offers luxury living at its finest. Bask in the spectacular view of the world famous Crescent beach on Siesta Key from this three (3) bedroom, three (3) bath beach front condominium's open air ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$324

avg/night

$324
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This adorable ground floor 1 bedroom unit in the Casa Mar complex on the beach side of Midnight Pass offers screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car. Tennisand Community laundry facilities. Beach chairs are provided by ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$478

avg/night

$478
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

**Any advertised discounts on website do not apply to this unit***Beautiful 7th floor beachfront condo in Crescent Arms North building. Screen lanai with beach views, washer/dryer right outside your door, elevator, heated pool, community grills and beach chairs provided by association. Located just about ...

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Property Type

Siesta Key Condo

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Siesta Key Villa
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3.5 bathrooms

$647

avg/night

$647
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Contemporary 3 Bedroom 3 Bath Luxury townhome. Beach views from the 3rd bedroom on top floor with full bath and bonus room and murphy bed. Master suite with tub and walkin shower, Gourmet kichen, leather furniture, balcony with partial views of the Gulf from the 3rd floor balcony. Laundry in unit, 2 car ...

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Property Type

Siesta Key Villa

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Siesta Key House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$624

avg/night

$624
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

***POOL CAGE IN PHOTOS IS NO LONGER AFTER HURRICANES*** ENJOY THIS 4 BEDROOM, 3 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA ISLES. OPEN FLOOR PLAN WITH LOTS OF SPACE, HARD WOOD FLOORS, WITH STUNNING VIEWS FROM EVERY ANGLE. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND WIRELESS INTERNET ...

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Property Type

Siesta Key House

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$277

avg/night

$277
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

SIESTA KEY.GETAWAY Experience a luxury condo with a view. Located on the world renowned Crescent Beach at Siesta Key. Gulf and Bay Club is a 32 acre resort community with exceptional beach access, top notch amenities and amazing sunsets. 6 pickle ball courts. 5 hard court, 1 clay tennis courts. Gym. ...

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Property Type

Siesta Key Condo

Featured review

"Perfect Stay for Relaxation and Fun!"

Our family had the pleasure of staying at this Gulf and Bay rental on more than one occasion. The condo is a hidden gem with a spectacular view, and just steps away from the beach. We could not have asked ...

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
1 review

$293

avg/night

$293
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

*** 20% OFF FOR WEEKLY RATES IN APRIL 2025*** ENJOY THIS SOUGHT AFTER GROUND FLOOR BAY VIEW UNIT WITH LARGE SCREENED LANAI OVERLOOKING THE CANAL. 2 TV'S W/DVD AND GORGEOUS POOL, TENNIS, WASHER DRYER IN UNIT. BEACH ACCESS RIGHT ACROSS THE STREET (NO BEACH CHAIRS OR EQUIPMENT PROVIDED) AND COVERED ...

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Property Type

Siesta Key Condo

Featured review

"Very Good Except"

We were given no access code for the tennis courts or pickleball courts. Unable to use because it was a SundaySome stole own personal noodles (2) that were on the Lanui. No lock on the Lanui.Washer ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$302

avg/night

$302
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

4TH FLOOR BAYSIDE, 2 BEDROOM / 2 BATH CONDO LOCATED IN THE CAPRI BUILDING OF THE EXCELSIOR COMPLEX. THE COMPLEX HAS 2 POOLS (ONE ON BEACHSIDE AND ONE ON BAYSIDE) WITH HOT TUB, 3 LIGHTED TENNIS COURTS, OUTDOOR BARBECUE / PICNIC AREA AND BEACH ACCESS. UNIT OFFERS WASHER / DRYER, HIGH SPEED INTERNET SERVICE, ...

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Property Type

Siesta Key Condo

Featured review

"2 hurricanes"

We were due to stay for 2 weeks from 26th sep unfortunately due to hurricane helene we weren't able to stay .siesta rentals returned all our sad but we will come ahain

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$293

avg/night

$293
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Harbor Towers 2nd floor unit located a few blocks south of the Siesta Public beach. Beautiful property located on the intercoastal. Pool and tennis, propane grills and coin laundry on each floor and elevator. NO smoking in unit and NO pets. Units sleeps 4, 1 King and 2 twins. 2 Week min. CLEANING FEE ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$614

avg/night

$614
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

BEAUTIFUL BEACHFRONT CONDO WITH VIEWS FROM LIVING ROOM AND BOTH BEDROOMS. BEACH CHAIRS PROVIDED ON THE BEACH. LARGE LANAI RUNS ENTIRE WIDTH OF UNIT. LEATHER FURNITURE, ONE OF OUR MOST POPULAR UNITS. BIG SCREEN TV, VCRand DVD, TV IN EACH BEDROOM. WASHER and DRYER IN UNIT. HIGH SPEED INTERNET ACCESS. (SIESTA ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
11 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

$180

avg/night

$180
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, ...

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Property Type

Siesta Key Condo

Featured review

"Absolutely gorgeous property"

Absolutely gorgeous property. The grounds and the property were kept beautifully. All of the amenities that were promised, were there. Being so close to the beach was a plus. There was no need to rent a ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$516

avg/night

$516
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

GORGEOUS GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE SOUGHT AFTER CRYSTAL SANDS COMPLEX. TILE FLOORS THROUGHOUT KITCHEN, BATHS and LIVING ROOM. 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH SPEED WIRELESS INTERNET ALSO AVAILABLE, (SIESTA 4-RENT IS NOT ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3.5 bathrooms

$553

avg/night

$553
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

ENJOY THIS 3 BEDROOM, 3 1/2 BATH UNIQUE PRIVATE HOME LOCATED ON TWO CANALS JUST EAST OF SIESTA VILLAGE. THE HOME WAS BUILT IN THE TRUE SARASOTA SCHOOL OF ARCHITECTURE DESIGN TO TAKE ADVANTAGE OF AIR FLOW AND LIGHT BUT ORIENTED SO THAT YOU NEVER HAVE DIRECT SUNLIGHT AT ANY TIME OF THE DAY. OPEN FLOOR PLAN ...

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Property Type

Siesta Key House

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$184

avg/night

$184
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Beautiful ground floor unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Unit sleeps 4, 2 Cable TV's , wireless internet ( Siesta 4 Rent is not responsible for tech support), community coin laundry right outside the door, covered parking, community pool ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 3 bathrooms

$537

avg/night

$537
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 3 BATH UPDATED POOL HOME LOCATED IN A BEAUTIFUL SIESTA KEY NEIGHBORHOOD. HOME OFFERS NEW FURNISHINGS, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, HIGH-SPEED INTERNET WITH BOOSTER, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). ENJOY THE LARGE PRIVATE ...

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Property Type

Siesta Key House

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$285

avg/night

$285
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

2ND FLOOR UNIT, COMPLEX OFFERS, POOL, WIFI AT THE POOL AREA ONLY. ( SIESTA 4 RENT DOES NOT OFFER TECH SUPPORT), NEAR SHOPPING, 2 BLOCKS TO THE PUBLIC BEACH ACCESS, END UNIT OFFERS A LITTLE MORE SPACE. 2 WEEK MIN. LAUNDRY FACILITY ON 1ST FLOOR. 1 King, 2Twin, 1SOFA BED. CLEANING FEE $185

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms

$466

avg/night

$466
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

PRIVATE 3 BEDROOM / 2 BATH HOME LOCATED IN A BEAUTIFUL RESIDENTIAL NEIGHBORHOOD. 1 MILE FROM THE WORLD FAMOUS SIESTA KEY BEACH. FULLY RENOVATED AND NEWLY FURNISHED FOR YOUR ENJOYMENT WITH AN OPEN FLOOR PLAN WITH LOTS TO OFFER. KITCHEN W/ STAINLESS STEEL APPLIANCES AND LARGE PANTRY. 3 LCD SMART TVS, DVD. ...

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Property Type

Siesta Key House

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
Studio | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 0 bedrooms, 1 bathroom

$243

avg/night

$243
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND POOLS. UNIT OFFERS A BRAND NEW QUEEN MURPHY BED, 32" LCD FLAT SCREEN TV, DVD / VCR AND CD PLAYER. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. COMPLEX ALSO ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$295

avg/night

$295
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Beautiful house on Siesta Key with private pool and generous space. 15 min walk to the beach! This charming 3-bedroom, 2-bathroom private home is located in discreet residential neighborhood, on the beautiful Siesta Key island. It offers a large fenced outdoor area, with a private pool, plenty of parking ...

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Property Type

Siesta Key House

Featured review

"great location to the Village and beach"

A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit ...

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Siesta Key Bungalow
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 0.5 miles to Siesta Beach access 7

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

Featured review

"My stay at the Canal Place in Siesta Bungalows"

I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$264

avg/night

$264
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This 1 bedroom , 2nd Floor unit in Siesta Village offers, great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 2 TV's. Complex offers community pool and laundry facilities located off common ...

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Property Type

Siesta Key Condo

Featured review

"Siesta Key paradise"

We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1.5 bathrooms

Distance to beach: 250 feet to Siesta Key

$213

avg/night

$213
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...

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Property Type

Siesta Key Condo

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Siesta Key Vacation Rentals

Monthly Rentals in Siesta Key

Your Ideal Monthly Rental Awaits

Explore a range of monthly rentals in Siesta Key, from beachfront condos to luxurious homes with ocean views. Whether you want to be close to Siesta Beach or prefer a quiet retreat near Crescent Beach, there’s a rental to suit your needs. Enjoy the comfort of a long-term stay in this coastal paradise.

Why Rent Monthly?

  • Cost-Effective: Monthly rentals offer lower rates compared to shorter stays, making them perfect for long-term vacations or work trips.
  • Home-Like Comfort: Fully furnished rentals provide kitchens, spacious living areas, and private bedrooms for the ultimate comfort during your extended stay.
  • Relax and Settle In: Unpack, unwind, and explore Siesta Key without the rush, making the most of your time in this beautiful location.
  • Live Like a Local: A longer stay allows you to experience Siesta Key’s unique charm, from its powdery white sands to its lively village scene.

Book Your Monthly Rental Today

Don’t wait to secure your ideal long-term rental in Siesta Key. Browse our listings and find the perfect property for your extended stay. Whether you’re looking to escape the cold or enjoy a warm, sunny vacation, Siesta Key is the place to be.

Plan Ahead for Future Stays

Booking in advance is the best way to ensure you get the rental you want, especially during the busy winter months when Siesta Key is in high demand.

Amenities and Perks for Long-Term Stays

  • Fully Furnished Rentals: Enjoy move-in-ready homes complete with fully equipped kitchens and comfortable living spaces.
  • Flexible Dates: Choose your move-in and move-out dates with ease, perfect for extended stays.
  • Transparent Monthly Pricing: Enjoy competitive rates with no hidden fees.
  • Remote Work Ready: Many rentals offer high-speed Wi-Fi and dedicated workspaces, ideal for remote workers.

Popular Amenities for Monthly Rentals

  • 🥘 Full kitchen
  • 📶 High-speed Wi-Fi
  • 🐾 Pet-friendly options
  • 💻 Workspace for remote professionals
  • 🚗 Free parking

Monthly Rentals in Siesta Key for Every Traveler

Group-Friendly Rentals

Planning a group vacation or family reunion? Siesta Key offers spacious rentals with multiple bedrooms and large living spaces, perfect for groups looking to enjoy a relaxed beach getaway.

Family-Friendly Monthly Rentals

Siesta Key is ideal for families with attractions like Siesta Beach, Point of Rocks, and Turtle Beach. Our family-friendly rentals provide ample space, outdoor areas, and proximity to kid-friendly activities like boating, snorkeling, and wildlife viewing.

Romantic Getaways for Couples

Siesta Key’s romantic sunsets and tranquil beaches make it a great destination for couples. Enjoy cozy monthly rentals with ocean views, private pools, and easy access to intimate dining and beachside strolls.

Winter Retreats for Snowbirds

Siesta Key is a favorite among snowbirds seeking to escape the cold northern winters. With its warm weather, stunning beaches, and a laid-back atmosphere, it’s no wonder snowbirds flock here each winter. Our monthly rentals provide a comfortable and convenient home base for an extended stay.

Why Siesta Key is Perfect for Snowbirds

  • Mild Winter Climate: Enjoy average winter temperatures in the 70s, making Siesta Key an ideal escape from the cold.
  • World-Class Beaches: Siesta Beach is consistently ranked among the best beaches in the world, offering powdery white sand and clear waters.
  • Active Lifestyle: Stay active with a variety of outdoor activities, including beach walks, biking, and water sports.
  • Community and Convenience: Siesta Key offers a welcoming community atmosphere with easy access to everything you need, from grocery stores to healthcare services.

Book Your Winter Stay Now

Don’t miss out on your chance to spend the winter in paradise! Reserve your long-term rental in Siesta Key today and enjoy everything this beautiful destination has to offer.

Outdoor Activities in Siesta Key

Siesta Key is known for its stunning beaches and outdoor adventures. Staying in one of our monthly rentals puts you close to:

  • Beaches: Relax on Siesta Beach, Crescent Beach, or Turtle Beach for sunbathing, swimming, and beachcombing.
  • Water Sports: Try kayaking, paddleboarding, or parasailing, with equipment rentals and tours available at the beach.
  • Fishing: Whether you’re casting from the shore or taking a fishing charter, Siesta Key offers excellent opportunities for anglers.
  • Nature and Wildlife: Explore local parks and nature reserves, such as the nearby Myakka River State Park, for hiking, birdwatching, and wildlife viewing.

Seasonal Information about Siesta Key Monthly Rentals

💰 Highest rates
December through March

🎉 Busiest month
February

🏠 Popular home types
Beachfront condos and single-family homes

🔥 Hottest months
July and August

❄️ Coldest months
January and December

Rainiest months
June through September

🌺 Best months for flowers
April and May

🌴 Peak tourist season
December through March

🍂 Quietest months
September and October

🌊 Best beach months
March through May

🏌️ Best golfing months
November through April

🎨 Top cultural events
Siesta Key Crystal Classic Sand Sculpting Festival (November), Siesta Fiesta Art Festival (April)

🍽️ Best dining months
January through March

🦋 Best months for nature activities
March through May

🛶 Best water sports season
June through September

🏖️ Best months for shelling
May and June

📅 Local festivals peak
November through April