Holiday rentals with a pool in Sanford

4.95 out of 5 average rating, 122 reviews

Home in The Villages

2/2 custom pool home with 4 person gas golf cart

Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

4.84 out of 5 average rating, 224 reviews

Home in Clermont

Great House w/Heated Pool;Near all Parks!

Welcome to la Casita de todos! This home will be your home away from home, children-friendly, and spacious for the whole family! Dogs under 20 pounds are allowed with a 75 USD fee per pet. HEATED pool with a charge fee of $ 25 USD per day. BBQ grill has an extra charge of $40 USD (for the whole stay, including 1 propane gas and cleaning). After booking and before check-in please let me know if you are bringing a pet or will use the BBQ. Locations nearby: Walmart 0.5 miles. Dollar Tree 0.1 miles.

4.92 out of 5 average rating, 118 reviews

#5744 LakeFront Two Master Suites Pool Spa Disney

Come & Relax in the beautiful Florida sunshine and enjoy all the conveniences this renovated house offers.The private home is located inside the famous Regal Oaks Resort, so you can use all the resort amenities at no extra charge! The best part - Disney World and other attractions are just a short drive away, making it perfect for families and fun lovers alike. 5 Min Walk to Old Town 8 Min Drive to Disney World 20 Min Drive to Universal Studios Experience Kissimmee With Us & Learn More Below!

Top Guest favourite

4.92 out of 5 average rating, 106 reviews

Hidden Treasure Pool Home - Sleeps 6 Very Comfy!

No cleaning fee charged!! You will love this beautifully decorated & SUPER CLEAN! Cozy Hidden Treasure home is where you can relax with very soft leather reclining sofas! The home sleeps 6 and is a 3 bedroom & 2 bath home with newly refinished glistening pool and easy to use door pool alarm. This home is in a family residential community and I have repeat guests that love to return here after having a great time! My home is very private and the yard is fenced all around. The Theme Parks Await!

4.88 out of 5 average rating, 115 reviews

Townhouse in Kissimmee

Stunning Disney Home w/Pool & Free Resort Access

Our property was featured in Travel Guide USA - 2025 Orlando Edition!! Welcome to our beautiful spacious home, featuring 3 king-sized bedrooms, 2 themed bedrooms, an entertainment loft and 4.5 bathrooms, which will comfortably accommodate three families. We are located in the upscale gated resort of Windsor at Westside with a 10,000 sq. ft. of state-of-the-art club house with a large pool, lazy river, water park, hot tub, gym, beach volleyball and basketball courts, restaurant & bar, arcade.

4.87 out of 5 average rating, 101 reviews

Home in New Smyrna Beach

Upscale Beach House walk to Flagler Ave & Beach

Upscale Beach living with a fantastic location. 2-minute walk to the beach and Flagler Ave. Beautiful home that features a private upstairs and downstairs unit with separate outdoor entrances. The pool area is a tropical paradise & has plenty of space to relax. This area is a shared space with the rental property next door. Requirement of 4-night min for this listing during peak season. Will accommodate shorter stays if available, please message us if trying to book for less than 4 nights.

4.86 out of 5 average rating, 7 reviews

Home in Davenport

Acres View 5bed/4bath near Disney. Own Pool & Spa!

Relax with the whole family at this peaceful place to stay. 5 bedrooms and 4 bath private villa with two living rooms . Close to Disney and all theme parks and also only moments to Posner park for the shopping enthusiast. Enjoy nearby events and all the parks yet come back to country views and rejuvenation at your private heated * pool and *spa! 35 to Orlando International Airport! * let us know at booking if you want pool/spa to be heated for $40/day. •BBQ available for cleaning fee of $65.

Top Guest favourite

Villa in Davenport

5 out of 5 average rating, 33 reviews

25 Minutes to Disney Parks!

Enjoy a perfect getaway in our modern, detached home located in a quiet gated community, just 25 minutes from Disney parks. Relax in the private pool and hot tub after a day of fun, or enjoy some friendly competition in the fully-equipped game room. With stylish interiors, spacious living areas, and all the comforts you need, this home is an ideal retreat for families and friends seeking both relaxation and adventure. Make lasting memories in a space that feels like your own!

4.92 out of 5 average rating, 36 reviews

Stunning Home with Pool Minutes to Disney!

Relax and unwind in this exceptionally appointed 4 bedroom home with tons of space for your family to enjoy. Fully stocked for your home away from home. Private heated pool (heat included). Large TV in family room, both master bedrooms and 2 family bedrooms. Cozy luxury accommodations. Game room with ping-pong table, basketball and foosball table. Wifi included for your convenience. Have fun with the whole family at this stylish place.

4.7 out of 5 average rating, 83 reviews

Home in Orlando

Rare Heated Pool House close to Downtown Orlando

Spacious ans stylish pool home close to downtown Orlando. Home is accessible to Many major highways including 408, I4, 429, turnpike and only 12 minutes from the Universe Studio. Regardless of long-term or short-term you will have an forgettable experience at this Luxurious pool home with a large patio equip with television outside. You can get the pool heated for an extra charge. Many restaurants and attractions nearby.

4.82 out of 5 average rating, 117 reviews

Pool House in Kissimmee

Quiet and spacious pool house in Kissimmee Florida, 20 minute away from Disney / Universal / Acquatica / SeaWorld theme parks. - 4 bedrooms - 2 bathrooms - Dining Room - Family Room - Kitchen - Double car garage - BBQ - Pool (heater optional) - Security Cameras Outside Only - WiFi 400 MBPS Pool Heater: If you want to use the heater please contact owner This will be your best vacation stay in Kissimmee / Orlando.