
Vacation 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.

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.

Beautiful pool home with golf cart by the beach
Welcome to this beautifully remodeled Home with golf cart, nestled within the idyllic community of Grove City in Englewood, Florida. This home offers two bedrooms and one bath, crafting an inviting haven suited for both small families and individuals in pursuit of comfort and ease. Notable features include a welcoming enclosed front porch and expansive back sunroom, alongside an attached one-car garage and a spacious backyard adorned with a convenient shed. With everything at your fingertips.

Your Coastal Getaway!
Your vacation home is on a peaceful street in a quiet neighborhood within an 8 minute drive of Englewood Beach and within 15 minutes of several other popular beaches. This home is convenient to shops, restaurants and famous Dearborn street. Property comfortably sleeps up to 6 guests with a fully furnished kitchen, 2 bathrooms, a lanai, Swimming pool and it is pet friendly! Relax with the whole family at this peaceful place to stay. Maximum of 2 PETS ONLY! PETS MUST BE 30 LBS or LESS.

January & February Now Available. Act Fast
Kick back and relax in this calm, stylish space. Every inch has been updated, upgraded, and designed with your comfort, relaxation, and enjoyment in mind. Lemon Bay is a special place on its own accord. When you add to it the magic the Tiki on the Bay Community adds to the mix, we believe you’ve found paradise. Tiki on the Bay is a small, inviting community that's perfectly located. You're just moments from multiple Gulf front beaches, Historic Dearborn Street, and fantastic restaurants.

Turtle Bay - minutes to Boca Grande!
Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

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.

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.

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, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach.

Private Heated Pool + Swim-Up Bar • Mins to Beach
Unwind in this thoughtfully designed 3-bedroom Florida retreat just 5 miles from Englewood Beach. Enjoy a private, heated pool with swim-up bar, screened lanai, and lush tropical privacy. Inside, you’ll find an open-concept living space, fully equipped kitchen, spa-style primary suite, and comfortable guest rooms. Ideal for families, couples, or friends seeking comfort, privacy, and easy access to beaches, golf, and dining.

Spacious 2 Bedroom Home | Near Beach | Heated Pool
This beautiful home just minutes from the beach offers 2 spacious king bedrooms, a queen sofa bed in the large open living area, and a full kitchen ready for entertaining. Gather your family around the dining room table for food and games and then relax on the lanai or have a float in the pool. The hosts provide Margaritaville frozen concoction machine, 2 bicycles, beach chairs, beach towels, shark tooth tools, and more.
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Iguana Alley, Beach HEATed Saltwater Pool on Canal

Englewood Escape: 3BR Waterfront with Pool

❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*

Dolphin Inn near Englewood Beach

Gulfstream Haven

Villa Sanddollar Awaits ! 1071HS

The Turtle Nest Pool Home

Heated SaltWater Pool + Only 2.5 mile to Beach!
Condo rentals with a pool

Ocean Oasis on Manasota Key - Ocean View

Location! Gulf Condo @ S. Jetty 30 day minimum

Manasota Key Condo Bay side Beach Access

Vacay on the Beach !

Spacious 2BR 2BA Beach Condo for Perfect Vacation

A little slice of paradise

Private Beach, Fishing Dock & Heated Pool Paradise

Waterfront Condo in Placida. THE location and Pool
Other vacation rentals with a pool

Heated Pool, Cozy 2 Bed-2 Bath House

Quiet Neighborhood ~ Waterfront Heated Pool!

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Tropical Oasis, pool, golf, dog friendly

CLEAN*Great Location*Dockage Available*HEATED Pool

1mi to Beach. 1+ acre of jungle Pool & Pickleball

Luxury Retreat: Oasis with Pool & Putting Green.

Peaceful waterfront home
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 172 | € 202 | € 211 | € 171 | € 150 | € 147 | € 150 | € 138 | € 133 | € 141 | € 142 | € 148 |
| 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 Englewood

Total vacation rentals
Explore 520 vacation rentals in Englewood

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

Verified guest reviews
Over 11,700 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wi-Fi availability
510 of Englewood vacation rentals include wi-fi 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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