Vacation rentals with a pool in Englewood

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Top-rated rentals with a pool in Englewood

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Englewood

5.0 out of 5 average rating, 35 reviews

Waterfront! Sunset Deck, Pier & FREE Boat Docking!

Welcome to Tiki In Paradise! Enjoy the tropical setting in this restored fishing cottage with direct Lemon Bay front cottage views! Sit back & relax and enjoy Lemon Bay water views from every window in our cottage! All the comforts you want and deserve. You will never find another property with the character, views & cleanliness like this special place. Completely remodeled. We are moments from Gulf front beaches, Historic Dearborn Street & fantastic restaurants! Private, Unique & Special!

Sep 9 – 16

G$30,237 GYD per night

Superhost

Guesthouse in Englewood

4.93 out of 5 average rating, 234 reviews

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.

Sep 15 – 22

G$69,308 GYD per night

Superhost

Home in Englewood

4.93 out of 5 average rating, 125 reviews

Stunning Home, Saltwater Heated Pool By the Beach

Stunning home meticulously maintained both inside & out. Follow the sunshine & salty air & arrive at your home away from home. Whether cooking for one or ten, the chef in the group is certain to appreciate this fully upgraded, open concept kitchen. Start the day brewing coffee in the Keurig & end the day sharing a bottle of chilled Pinot from your wine fridge. Open the sliders & the party extends outdoors. Inflate the raft & spend your days daydreaming afloat in the heated, salt water pool.

Oct 3 – 10

G$35,534 GYD per night

Guest favorite

Guesthouse in Englewood

4.97 out of 5 average rating, 202 reviews

Shabby chic cottage with pool one mile from beach

This adorable shabby chic decor style studio cottage for 2 is located on one acre of old Florida landscaping. Great area for walking, biking, for exercise. Included with this home is access to a pool and large, lovely lanai, just outside the door. Head south for 7 min to historic Dearborn St or north for 3 miles to Venice. This location offers peace and tranquility combined with accessibility to endless activities nearby. 2 twins OR one King, per your preference. The pool is unheated.

Apr 16 – 23

G$28,272 GYD per night

Guest favorite

Home in Englewood

4.79 out of 5 average rating, 149 reviews

Custom Built Manasota Beach Home with Pool

Custom built large home only 2.5 blocks to Manasota Beach. Most guests walk and a beach wagon(pull behind for beach gear)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.

Oct 13 – 20

G$48,718 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 28 reviews

Relax at La Perla Pool Home - Heated Pool

Welcome to our beautiful, 2bed 2 bath house in Englewood, Florida! Immerse yourself in style & comfort as you step into La Perla. With its modern decor, this house offers the perfect blend of relaxation and style. The bedrooms are furnished to provide a peaceful haven after a day at the beach. Just a quick 10-minute drive from the beach. Whether you're enjoying the pool or exploring the pristine beaches of Manasota Keys, our house offers a delightful escape from the everyday.

Jul 17 – 24

G$30,874 GYD per night

Guest favorite

Condo in Englewood

4.89 out of 5 average rating, 54 reviews

Manasota Key Unit 20B across from private beach

Welcome to Peekaview 2. A Spacious young condo in the heart of Manasota Key with private beach and bay access! Kitchenette includes dishwasher, micro, refrigerator, toaster oven/coffee maker. (No stove) and Washer/dryer. Balcony with partial views of the bay! Boat docks avail. (no trailers allowed) Heated Pool (Nov-April) Walk to island restaurants and amenities (1 upscale restaurant next door!) Bright and updated throughout! Max guests 2 NO PETS: NO SMOKING: NO VAPING

Aug 29 – Sep 5

G$30,237 GYD per night

Guest favorite

Condo in Englewood

4.93 out of 5 average rating, 114 reviews

Immaculate Ground Floor Beach Studio on the Gulf

Please note: This complex had minimal damage, but you may see remnants of the hurricane in the complex. There is a protective tarp on the roof of my building even though there was very few tiles that blew off in the storm. There is a separate, beachside building with the same protective tarp & is getting new stucco on the west side facing the beach. You do not see the face of this building from my property as my place faces the pool. *See my pictures for more details*

May 15 – 20

G$35,419 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 24 reviews

Pool Home

A gorgeous, fully furnished 3 beds, 2 baths, Pool (not heated) home in a safe, quiet, friendly neighborhood. Centrally located near shops, popular restaurants, the Cove of Rotonda golf center, fishing, water sports, Englewood Beach, Boca Grande, Mineral Spring, Sunseeker resort, Wellen park, Charlotte sports park! ** Out of consideration for other Guests with Allergies. No Pets, No Smoking allowed, No exception! Thank you! Early check-in available upon request.

Jul 24 – 31

G$32,167 GYD per night

Guest favorite

Home in Englewood

4.92 out of 5 average rating, 90 reviews

Casa Blu: Serene Pool Villa, Close to Beach

Welcome to Casa Blu, your cozy retreat in Florida's sun-kissed paradise. Close to restaurants, parks, and beaches, and Old Englewood. Just 7 miles to Englewood Beach. The stresses of daily life melts away with its single-floor layout, comfy bedrooms with private baths await. Enjoy fast WiFi, Smart TVs, and a fully equipped kitchen. Unwind on the screened lanai or take a dip in the private saltwater pool. Everything's covered, from beach gear to a pack 'n play.

Dec 3 – 10

G$27,740 GYD per night

Guest favorite

Villa in Englewood

4.92 out of 5 average rating, 111 reviews

Magnificent Waterfront! Kayaks-Pool-Beach! gs

Fantastic Manasota Key Location! Upstairs at Blue Island Inn, waterfront “Seaglass Villa” dazzles with spectacular Bay views! 2 cozy bedrooms; 1 bathroom, kitchen & 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!

Oct 20 – 27

G$32,654 GYD per night

Guest favorite

Condo in Englewood

4.89 out of 5 average rating, 116 reviews

A Beautiful Sunset Awaits - Steps to Beach

This recently constructed condo is shiny new and only a one block walk to the beach. Lemon Bay is even closer with first come, first serve boat docks. Sunny one bedroom condo has a well appointed kitchen, and washer & dryer in the unit. Swimming pool and grill area are only a few feet outside the front door. King size bed, and sleeper sofa. Free, shaded parking.

Aug 13 – 20

G$36,817 GYD per night