Holiday rentals with a pool in Osprey

4.88 out of 5 average rating, 163 reviews

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

4.97 out of 5 average rating, 94 reviews

3 bedroom Heated salt water pool close to Siesta

Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

4.97 out of 5 average rating, 32 reviews

Right on the bay! Heated pool! King bed

Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. You will have whole house except two rooms which will be locked and no one will be there. One bedroom with a king size bed and sleeping sofa in the family room (if more than two guests coming). Full size kitchen, two family rooms, pool and gorgeous view on the salty bay for nature lovers.

5 out of 5 average rating, 28 reviews

Home in Nokomis

Lake View, 6 Miles From Beach

-Located inToscana Isles (gated community with heated infinity pool, gym, tennis/pickleball/bocce ball courts, playground, dog park, billiard room, and monthly events) -Backs up to 1 of 3 lakes (kayaking and fishing allowed, 2 kayaks, 2 fishing poles and tackle box included) -6 Miles from Nokomis Beach, 6.8 miles to Venice and dog beach, the only pet friendly beach in the area (4 beach chairs, umbrella, cooler, wagon and beach bags included) -Close to Legacy Trail and Oscar Scherer State Park

5 out of 5 average rating, 12 reviews

Villa in Osprey

Paradise with a pool, pier and private beach area

Intercoastal, Blackburn Bay waterfront home with boating facilities near Casey Key and Siesta Key. On a point facing the setting sun. This is simply paradise. The pier is long, and the water deep enough to handle most boat docking needs. The large, heated pool is a few steps from the screened lanai and the deck beckons "come watch the sunset". And while it won't replace one of the large beaches on the key, you can lay or play on our beach hidden by mangroves, and easily launch kayaks, etc.

4.86 out of 5 average rating, 35 reviews

Luxury 6BR Retreat with Beach Access

Experience the ultimate Siesta Key lifestyle in this luxurious 6BR coastal retreat. - Private pool and spa with deeded beach access - Smart home features and gourmet kitchen - Spacious game/workout room and movie theater - 10 ft. ceilings in the kitchen and 12 ft. in the living room - Master bedroom with walk-in closet and luxurious bath - Lush tropical landscaping and outdoor fire pits - Exceptional Siesta Key Oasis with 6 Bedrooms, Deeded Beach Access, and Luxury Amenities!

4.93 out of 5 average rating, 369 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the pool and patio (renovated in July 2025) and comfy outdoor furniture in your fenced in backyard where you can bask in the sun. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

4.97 out of 5 average rating, 144 reviews

Home in North Port

Cozy & Beautiful Pool Villa in Sarasota County, FL

Welcome to our home! It’s our pleasure to host you! Your family & friends will be close to everything when you stay at this centrally-located place: shopping, dining, beaches, entertainment, Warm Mineral Springs, Aquatic Center, etc. This charming house located in a beautiful & quiet neighborhood, tastefully furnished & decorated, fenced for your privacy & perfect for making memories with family & friends. Plenty of amenities to make your stay as comfortable as possible. Great location.

4.94 out of 5 average rating, 126 reviews

Home in Nokomis

Sunny Getaway/Beautiful House/Beach/Heated Pool

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

4.98 out of 5 average rating, 54 reviews

Home in Nokomis

The Pineapple Escape

The Pineapple Escape is the perfect gateway vacation house that has everything you're looking for. With a heated pool for access year round and beautiful kitchen for all your desires. Just a short drive from some of Florida's finest beaches, such as Nokomis Beach on Casey Key,Venice Beach and about 15 minutes drive to #1 beach in US, Siesta Beach in Sarasota,. You'll find this neighborhood to be quite serene and peaceful. Book today to start making memories at The Pineapple Escape.

Home in Indian Beach-Sapphire Shores

4.94 out of 5 average rating, 125 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

Superhost