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

Entire Beachside Condo! Don’t worry Beach Happy!
BOOK HERE!!! STEPS TO WORLD FAMOUS Manasota Key BEACH, FREE PARKING. Private beach access. WALKING DISTANCE TO MANY RESTAURANTS. 2 Bedroom, 1 Bathroom, beach themed condo with HEATED POOL access across street. Complimentary grill and Gulf sunsets. Your morning coffee is on us! Beach chairs, towels, and sand toys supplied. Kitchen is updated with filtered water, ice, and utensils supplied. Master Bedroom has a queen sized bed, pull out drawers and fireplace. Boat dock slip available upon request.

Coastal Retreat Villa with pool • near beaches
🌴 Escape to your getaway in sunny Englewood, Florida! Whether you're a couple seeking romance, a solo adventurer, a business traveler, or a family with kids, our home is designed for comfort & relaxation. Nestled in a prime location, it's the ideal home base to anyone looking to unwind and explore. Indulge yourself in this executive cozy, built from the ground in 2018 & featuring 3 bedrooms, 2,5-bath house with a Large (seasonally) heated swimming Pool (heating $ included during colder months)

Gulf front romantic cottage in paradise
Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Manasota Beach Home w/Pool. Steps To The Beach
Custom built large home only 2 blocks to Manasota Beach. Most guests walk and a beach wagon is provided. Located in a quiet neighborhood with easy access to downtown Venice and Englewood. Very large and private lot with beautiful mature palms! The home has tray and soaring vaulted ceilings. The whole home opens up onto the pool area with sliders in every room. The bedrooms are configured in a split style with the very large master suite being totally private. Rare beach home for rent left!

*New Listing* ☀️TheAquaOasis🌴Pool-6 miles to beach
Welcome to the Aqua Oasis! This home was built in 2020 and located just 6 miles to multiple beaches in sunny Englewood, FL! The home consists of 3 bedrooms & 2 full baths, an option to heat the outdoor pool, relaxing outdoor chairs around a gas fire pit, fenced in back yard to let your pets roam, and a gas grill to whip up your favorite meals! If your family desires your own, private space and private pool, but you want close proximity to local beaches- THIS IS FOR YOU!

Studio, pool, private beach, boat dock shark teeth
Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, full sofa bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach. Close to everything!!

Island Home & Casita, Pool, Golf Cart, Beach
Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

Exceptional Bay Views!
Fantastic Manasota Key Location! Upstairs at Blue Island Inn, waterfront “Seaglass Villa” dazzles with spectacular Bay views! 2 cozy bedrooms; 1 bathroom, kitchen & 1 cozy family room. On-site resort pool overlooks stunning Lemon Bay. 5-minute walk to ocean-side beach or enjoy “Bay-front beach” out back. Quiet island street. low-key quiet respectful vacationers. 1 car parking spot. No visitor parking. No boats. No pets. No smoking. Free use of kayaks!

Manasota Key
Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

Paradise on the Bay
Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.

Sunburst Condo - Beach, Bay & Pool
This Gulf-side Sunburst condo puts you right where you want to be—steps from the beach, moments from the bay, and an easy stroll to Dearborn Street for weekly farmers markets, local events, dining, and live music. Whether you’re beachcombing for shark teeth, relaxing poolside, or enjoying sunsets over the Gulf, this cozy island retreat delivers the best of Manasota Key living.

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!
BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!
Popular amenities for Manasota Key rentals with a pool
House rentals with a pool

Green Bamboo - saltwater pool, great backyard.

The Windsor @ Englewood Beach

Englewood Cottage with Pool, Hot Tub, and Fire Pit

#6/7) 30 Seconds To Beach Path! Bikes/Kayaks/Sups!

Beach Amore | Ocean front | 365 Sunsets a Year

Englewood 3 Bedroom Private Pool+Spa on Lemon Bay

Shoreview Bay House

Stunning/Private Beach Access/Heated Pool/Dock
Condo rentals with a pool

6 Siesta Breakers - Condo, Ocean View, Heated Pool

The Honeymoon Suite on Siesta Key Beach

On the Beach; Siesta Key SunBum Studio

Sarasota Surf & Racquet Club Siesta Key Condo

Bay Life @ManasotaKeyCondos

Siesta Key Beach Front Condo

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Cottage on Siesta Key Beachside & Stunning sunsets
Other vacation rentals with a pool

Cozy Venice Retreat w/ Private Pool • Near Beach

Beautiful Bayfront Condo

Steps to Water! Beach to Bay, Penthouse!

Villa Sanddollar Awaits ! 1071HS

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Boardwalk Beach Condo on Englewood Beach, Florida

Boca Grande Beach Cottage

21B Gulf Front 2/1.5
When is the best time to visit Manasota Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $285 CAD | $341 CAD | $362 CAD | $306 CAD | $251 CAD | $246 CAD | $234 CAD | $221 CAD | $225 CAD | $239 CAD | $225 CAD | $246 CAD |
| 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 Manasota Key

Total vacation rentals
Explore 280 vacation rentals in Manasota Key

Nightly prices starting at
Manasota Key vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 6,060 verified reviews to help you choose

Family-friendly vacation rentals
220 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wifi availability
280 of Manasota Key vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Manasota Key rentals

4.8 Average rating
Manasota Key stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Havana Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Four Corners Vacation rentals
- Condo rentals Manasota Key
- House rentals Manasota Key
- Family-friendly rentals Manasota Key
- Rentals with a washer and dryer Manasota Key
- Rentals with beach access Manasota Key
- Waterfront rentals Manasota Key
- Rentals with a hot tub Manasota Key
- Apartment rentals Manasota Key
- Rentals with outdoor seating Manasota Key
- Rentals with a patio Manasota Key
- Beach condo rentals Manasota Key
- Rentals with a kayak Manasota Key
- Beachfront rentals Manasota Key
- Villa rentals Manasota Key
- Beach house rentals Manasota Key
- Rentals with lake access Manasota Key
- Rentals with a fireplace Manasota Key
- Cottage rentals Manasota Key
- Rentals with a firepit Manasota Key
- Pet-friendly rentals Manasota Key
- Rentals with pools Charlotte County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- Bean Point Beach
- Coquina Beach
- Anna Maria Island Beach
- Turtle Beach
- Lido Key Beach
- Caspersen Beach
- Cortez Beach
- Anna Maria Public Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Lovers Key Beach
- Englewood Beach
- Lakewood National Golf Club
- Img Academy
- Myakka River State Park
- Stump Pass Beach State Park
- Blind Pass Beach
- Marie Selby Botanical Gardens
- North Jetty Beach
- Florida Gulf Coast University




