Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

2 bedrooms·2 baths
Longboat Key • Florida

8.425,50 $ USD gesamt für 60 Nächte

23. Okt. – 22. Dez. 2026

Heated pool & spa
Bathroom 1 bath/shower
Bathroom 2 walk in shower
Bedroom 1
Bedroom 3

Heated Pool & Spa 3bd/2bth, near Siesta Key Beach

3 bedrooms·2 baths
Sarasota • Florida

810,00 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

2 bedrooms·2 baths
Sarasota • Florida

31.480,00 $ USD gesamt für 120 Nächte

23. Okt. 2026 – 20. Feb. 2027

Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa
Fun in the sun starts here - Hosted by RentAnnaMaria
Sunset Views from Shore to Please! - Hosted by RentAnnaMaria
Shore to Please - Hosted by RentAnnaMaria
Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths
Anna Maria • Florida
5(13 reviews)

3.059,78 $ USD gesamt für 4 Nächte

8.–12. Nov. 2026

Palmetto House
Palmetto House
Palmetto House
Palmetto House
Palmetto House

Palmetto House

3 bedrooms·3 baths
Sarasota • Florida

2.230,86 $ USD 2.036,45 $ USD gesamt für 7 Nächte

9.–16. Nov. 2026

Comfortable sleeper sofa for guests while immersed in the tranquil ocean vibe!
Wonderful open space living area to relax and watch your favorite game or a good movie!
Have a picnic right on the water with the breathtaking view!
Enjoy your morning coffee and breakfast at the open concept dining area.
The bay beach in the community is a day of fun and sun!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths
Ruskin • Florida

658,35 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Comfortable sleeper sofa for guests while immersed in the tranquil ocean vibe!
Wonderful open space living area to relax and watch your favorite game or a good movie!
Enjoy your favorite movie or watch your favorite team on this nice smart TV and relax!
Enjoy your morning coffee and breakfast at the open concept dining area.
Breathtaking views off the living area!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths
Ruskin • Florida

641,87 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Cozy coastal living with Smart TV & relaxing vibe
Lido Beach Pool & Pavilion, The 25-meter lap pool is open Friday through Sunday, from 10:00 am to 4:30 pm, weather permitting. Fees apply.
Primary queen suite with private ensuite and plenty of natural light
Lido Key Beach
Sunny dining area for morning coffee or family dinners

Lido Key | Steps to Beach, Walk to St. Armands

2 bedrooms·2 baths
Sarasota • Florida
4.97(39 reviews)

1.282,00 $ USD gesamt für 3 Nächte

8.–11. Nov. 2026

Main living room with ample seating, dining today and bright sunshine gracing the windows.
Move the additional seating over to the couch after sitting down for dinner.
Lido Key Beach
Dinner for 4. Quick and easy access to the full size kitchen for home cooked meals while on vacay.
Queen bed, with additional ceiling fans if you like it really cold and of course your very own private full bathroom. Also, ample closet space to fully stretch out.

Lido Key Beach Escape | 2 Private Suites

2 bedrooms·2 baths
Sarasota • Florida
4.95(21 reviews)

1.862,55 $ USD gesamt für 3 Nächte

7.–10. Nov. 2026

FlipFlopsOn III Vacation Rental • 3 Blocks to the water • FL’s Gulf Coast • Sleeps 6
Your boutique Mediterranean-style 2BR bungalow (4 beds) — resort level comfort + coastal charm!
Your own private resort — located on a serene palm-lined lain in Sarasota’s coveted coastal district!
Half a mile to the Siesta Key, home of Siesta Key Beach — experience the sugar white sands of America’s #1 beach!
A Mediterranean-meets-California retreat where natural textures and curated details invite beautiful living

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath
Sarasota • Florida
5(2 reviews)

2.248,70 $ USD gesamt für 7 Nächte

24.–31. Okt. 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bedrooms·4 baths
Sarasota • Florida
5(2 reviews)

11.383,59 $ USD 10.850,06 $ USD gesamt für 7 Nächte

19.–26. Dez. 2026

Heated Saltwater Pool
The pool and surrounding area features enough lighting to enjoy the Florida evenings in style!
Catch the game on the 75" TV from the HOT TUB!
Newly remodeled kitchen with new stainless steel appliances (refrigerator, induction cook top, built in microwave/oven and dishwasher).
Living Room featuring a large sectional sofa and a 55" smart TV. Sit and enjoy the abundance of natural light.

The Funky Fish House

2 bedrooms·2 baths
Sarasota • Florida
4.99(156 reviews)

1.603,85 $ USD gesamt für 5 Nächte

28. Okt. – 2. Nov. 2026

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 1
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 2
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 3
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 4
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 5

Lovely room 5 miles from Siesta Key w/ Pool & Spa!

1 bedroom·1 bath
Sarasota • Florida
4.87(60 reviews)

225,00 $ USD gesamt für 3 Nächte

1.–4. Nov. 2026

Cozy Room 5 miles from beaches! image 1
Cozy Room 5 miles from beaches! image 2
Cozy Room 5 miles from beaches! image 3
Cozy Room 5 miles from beaches! image 4
Cozy Room 5 miles from beaches! image 5

Cozy Room 5 miles from beaches!

1 bedroom·1 bath
Sarasota • Florida
4.95(75 reviews)

225,00 $ USD gesamt für 3 Nächte

1.–4. Nov. 2026

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ Nacht(zzgl. Gebühren & Steuern)
Welcome to your private paradise just minutes from the beach—where relaxation begins the moment you pull in.
Big group? No problem. Our extendable dining table fits up to 10—perfect for family feasts, card nights, or celebratory toasts.
Get the best of both worlds: soft and firm pillows, a private ensuite, blackout blinds for restful sleep, and a king bed made for unwinding. Plus, a smart TV for ultimate relaxation.
When the beach is a few blocks away but the pool is right here. Welcome to the best of both worlds.
Skip the restaurants (if you want to). This kitchen’s got everything: oven, microwave, fridge, dishwasher—even a TV so you don’t miss a moment.

Siesta Key Home | Heated Pool, Theater & Arcade

4 bedrooms·3 baths
Siesta Key • Florida
5(36 reviews)

3.645,69 $ USD gesamt für 3 Nächte

25.–28. Okt. 2026

Heated pool
Siesta Key beach
Dusk view of front of building
Front door and porch area
Front door and sliding glass doors

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath
Sarasota • Florida

890,90 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths
Siesta Key • Florida
5(26 reviews)

14.950,00 $ USD gesamt für 28 Nächte

15. Apr. – 13. Mai 2027

Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Front of house.
Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Beautiful day at the beach

Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach

2 bedrooms·2 baths
St. Pete Beach • Florida
4.99(71 reviews)

4.173,38 $ USD 3.586,60 $ USD gesamt für 7 Nächte

11.–18. Nov. 2026

Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Beach. Steps from the cottage

Pass-a-Grille Gulf Front Cottage, Ocean View

1 bedroom·1 bath
St. Pete Beach • Florida
4.85(27 reviews)

7.476,17 $ USD 6.392,55 $ USD gesamt für 28 Nächte

1.–29. Dez. 2026

Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

1 bedroom·1 bath
Sarasota • Florida
5(71 reviews)

427,00 $ USD gesamt für 3 Nächte

25.–28. Okt. 2026

Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

2 bedrooms·2 baths
Sarasota • Florida

722,00 $ USD gesamt für 3 Nächte

25.–28. Okt. 2026

2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 bedrooms·2 baths
Sarasota • Florida
$100/ Nacht(zzgl. Gebühren & Steuern)
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bedrooms·2 baths
Siesta Key • Florida
5(2 reviews)

13.392,70 $ USD gesamt für 14 Nächte

12.–26. Dez. 2026