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

Suite Sun
*HEATED SOLAR POOL* Welcome to your tropical oasis in Englewood, Florida! Step outside and prepare to be amazed by the stunning outdoor space. The inground solar panel heated pool beckons you to take a refreshing dip on warm Florida days. Imagine sipping your favorite beverage as the sky transforms into a canvas of vibrant colors each evening. For the fishing enthusiasts, a private dock awaits your arrival. Cast your line and enjoy the serenity of the lake, all from the comfort of your backyard.

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.

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.

Steps to Water! Beach to Bay, Penthouse!
• Beach to Bay Penthouse: The best of both worlds • Spacious Layout: 2 bed/2 bath, open floor plan, soaring ceilings • Bright & Fresh: Newly painted, remodeled, bright windows • Prime Amenities: Heated pool, dock, beach access • Kitchen: Granite countertops for a sleek cooking experience Bedrooms: One with a porch & water view, another with its own bath Great Location: Walk to Magnolia’s on the Bay, restaurants, music, shopping, beach Outdoor Space:Large screened-in lanai, washer/dryer

Gulf Front Escape + Beach Access, Pet Friendly
🦩 Exclusive Amenities Include: • Walk Out to the Beach – Just Steps from Your Door • Historic Old Florida Charm • Coastal and Surf Decks with Outdoor Seating • Community Pool with Picnic Tables and Chaise Lounges • Community Grills and Post-Beach Outdoor Showers • Free WiFi and TV • Full Kitchen, Wares • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs and Umbrellas Provided • Tub/Shower Combo in Bathroom • Desk and Chair in Unit, Community Laundry

Pebble House w/ Screened Pool, Horseshoes, & more
Welcome to our serene retreat in Englewood—one of Florida’s true hidden gems. This beautifully maintained, well-appointed home offers a peaceful escape for families and couples alike. Set in a quiet, walkable neighborhood, the home features a newly screened private pool and is ideally located near the beaches, dining, and boating of Manasota Key, as well as the natural beauty of Myakka State Forest. Additional amenities include 2 bicycles, horseshoe pits, outdoor dining, 65” 4KTV, and more.

Gulfstream Haven
Welcome to Gulfstream Haven, a 1700 sf 3 bedroom 2 bath pool home conveniently located 8 minutes from Englewood beach with many shops and restaurants nearby. The home features a king size bed in the master bedroom, 2 singles in 1 bedroom and a king size in another. There is a double sleeper sofa in the family room for 2 extra guests. All bedrooms feature walk in closets. The large screened-in lanai has plenty of seating for all occupants, with direct access to the guest bathroom.

Green Bamboo - saltwater pool, great backyard.
Welcome to Green Bamboo, the charming and cozy vacation rental located in the beautiful Englewood, Florida! With its prime location, Green Bamboo is the perfect place to explore all that the area has to offer, from the most amazing beaches in the US to world-class golf courses and spectacular sunsets. Home is situated in a peaceful and gorgeous neighborhood. Just a short drive away (5 miles) you will find beautiful beaches, boat rentals and vibrant shopping and dining options.

Relaxing Poolside Retreat-min to beach-heated pool
Welcome to the Poolside where you can relax and unwind in this well-equipped 2-bed, 2-bath pool house just minutes from the beach. Enjoy a private heated pool (Sep-Apr), a fully stocked kitchen, a gas grill, 2 king bedrooms, a brand-new queen sleeper sofa and everything you need for a stress-free stay. We provide all beach gear so you can make the most of your time by the Gulf. Perfect for couples, families, or friends looking for comfort and convenience in a great location.

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!!

Paradise Palms Retreat
Discover our Paradise 3-bedroom, 2-bathroom Palms Retreat. Embrace the beach vibes, perfect your golf swing, reel in the excitement of prime snook and tarpon fishing spots or relax by the inclusive private pool. A short drive away is the Tampa Bay Rays Stadium. Stay seamlessly connected with our high-speed 1 Gbps fiber internet, ideal for streaming or remote work. Your perfect blend of comfort and convenience awaits in this relaxing Florida getaway!

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.
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Island Home & Casita, Pool, Golf Cart, Beach

3 Bedroom Home | Heated Pool | Close to Beaches

Peaceful waterfront home

*New Listing* ☀️TheAquaOasis🌴Pool-6 miles to beach

Englewood retreat (New heated pool +Spa

Heated Pool • Pool Table • Pac-Man • BBQ • 2 Kings

Villa Sanddollar Awaits ! 1071HS

Newly renovated home on canal with salt water pool
Apartment rentals with a pool

Location! Gulf Condo @ S. Jetty 30 day minimum

Vintage Villa, Thirty-Five

Spacious 2BR 2BA Beach Condo for Perfect Vacation

Gulf side condo be on the beach in minutes!

Private Beach, Fishing Dock & Heated Pool Paradise

Burnt Store Marina- 2BR w/ pool, marina, gulf view

Island Getaway Pool-Ferry-Grocery Delivery Incl.

Sunrise Over the Bay
Other holiday rentals with a pool

A Perfect Escape Near the Beach (Pet friendly)

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Family Fun-Relaxing Home w/heated Pool & Game Room

The Mangrove House

Venice Island villa/ walk to beach/ Swimspa-pool

Ultimate Luxury:Spa/Pool/Outdoor Kitchen/Firepits

#6) 30 Seconds To Beach Path/Tiki Bar/Bikes/Kayaks

Cozy beach house with pool
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £147 | £172 | £180 | £146 | £128 | £126 | £128 | £118 | £114 | £114 | £123 | £134 |
| 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 holiday rentals with a pool in Englewood

Total holiday rentals
Explore 580 holiday rentals in Englewood

Nightly prices starting at
Englewood holiday rentals start at £29 per night before taxes and fees

Verified guest reviews
Over 11,960 verified reviews to help you choose

Family-friendly holiday rentals
480 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wifi availability
580 of Englewood holiday rentals include wifi access

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

4.9 Average rating
Englewood stays are highly rated by guests – averaging 4.9 out of 5!
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