
Vacation rentals with a pool in The Meadows
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in The Meadows
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Siesta Key, FL - Casa Berano
Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs

The Sand Castle - Backyard Oasis Mins from Siesta!
*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want! Please message me if bringing 2+ pets

Green Jacaranda AMI Duplex A, 5 min walk to beach
Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

Luxury oasis in Sarasota
Welcome! In our luxury 2 bedroom, 2 bathroom home you will find yourself centrally located, and minutes from the best attractions Sarasota has to offer. This luxury condo is located in a quiet, safe, and private community with security. Free parking available to guests. Pool, gym, spa as well as a kayak/paddle board launch ramp available to guests. Minutes to Main street, Marina Jack, St. Armand's Circle, Sarasota Opera house, Marie Selby Gardens, farmer's market, Siesta key and Lido beach!!

Magical Guesthouse 1 mi from SRQ airport
@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Summer House longboat key
Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Tropical Oasis Heated Pool Hot Tub Near Siesta Key
Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

Your Private Retreat w/ Heated Pool
Welcome to your perfect Sarasota escape. Soak up the Florida sunshine and enjoy unforgettable coastal moments just minutes from your door. Nestled in one of Sarasota’s most sought-after neighborhoods, this charming home offers the ideal blend of peaceful relaxation and everyday convenience. Only 18 minutes from the world-famous Siesta Key Beach—known for its powdery white sands and crystal-clear waters—you’ll be perfectly positioned to unwind, explore, and make lasting memories.

Beach, Village, Dock & Private Pool! One-of-a-kind
Fully Restored Post-Hurricane and Ready to Welcome You!! RCC in Siesta Key is a one-of-a-kind coastal cottage perfectly located between the beach, canal, and village. Enjoy a private heated pool, private dock, and one of the best locations on the island. This 1,500 square foot standalone bungalow has been fully restored with fresh post-hurricane updates. If you want a charming, private beach home with no shared walls and no condo feel, you have found the right place!

Private Heated Pool Casita Near Downtown & Beaches
Built in 1925, Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴 Cert# VR24-00152

The Seabreeze Cottage with peaceful water views
Welcome to my newly renovated townhouse! The Seabreeze Cottage is a two bedroom, 1.5 bath, colorfully decorated townhouse with a fun beachy vibe! It has beautiful and peaceful water views of the lake. It’s within 30 minutes of the Gulf Coast’s best beaches, including Anna Maria Island, Longboat Key, and Siesta Key. Only ten miles from Sarasota airport (SRQ) and about one hour from Tampa airport (TPA).

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR
Bright second-floor 1-bedroom condo in a quiet residential area of Sarasota. Siesta Key Beach is a 5–10 minute drive (traffic dependent). Pet-friendly home — all pets welcome with a flat $10 pet fee per reservation, regardless of the number of pets. Guests enjoy access to a heated community pool and a convenient location close to shopping and dining.
Popular amenities for The Meadows rentals with a pool
House rentals with a pool

Beach Escape+Downtown | large yard/Heated pool

Coastal Comfort Getaway, Heated Pool!

Oceanfront Home with Heated Pool in Fishers Haven

Luxury Canal-Front Home + Heated Pool Near Beach

Lovely 3/2 home, 1 MILE to SK, intact after storm

Sarasota Paradise/Stunning Home/Heated Pool

Sunshine House- Sarasota Pool Retreat

Luxury Family Pool Home Near Siesta Beach
Condo rentals with a pool

Private Beach & Intracoastal Waterfront

Sea Shell Ocean View On Beach Walk Everywhere Pool

Crystal House on Siesta Key Beach

On the Beach; Siesta Key SunBum Studio

Beachfront Resort, Ocean View, Pool, Tennis, Gym

New Luxury 3/3 Condo in Margaritaville Resort

Sarasota Surf & Racquet Club Siesta Key Condo

Sun-Kissed Memories: Open Tomorrow, $225/nt+Fees!
Other vacation rentals with a pool

The Palms Away

Beachfront at Siesta Breaker | 2nd Fl | Gulf Views

Pool Home Oasis in Sarasota

Remodeled Mid-century POOL house

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches

Amazing beach view! Entire unit renovated!

Amazing Location! 30% off monthly stays!

Private Heated Pool Retreat for Two Families
When is the best time to visit The Meadows?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 103 | € 108 | € 108 | € 69 | € 64 | € 64 | € 65 | € 64 | € 65 | € 60 | € 65 | € 68 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about vacation rentals with a pool in The Meadows

Total vacation rentals
Explore 50 vacation rentals in The Meadows

Nightly prices starting at
The Meadows vacation rentals start at € 34 per night before taxes and fees

Verified guest reviews
Over 200 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of The Meadows vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across The Meadows rentals

4.9 Average rating
The Meadows stays are highly rated by guests—averaging 4.9 out of 5!
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